Circles and Curveballs
by dawdler
Summary: Post-Revival Rory Gilmore made a drastic decision to hide her pregnancy from Logan. Now 16 years later, Rory has been settled in a routine and content life with her son and boyfriend. She seems to complete the circle like her mother, but life always throws curveballs at you which throw you off the predestined course. Mostly told from Rory/Logan POV


**Introduction**

This happens 16 years after the revival, Rory hasn't told Logan about her being pregnant with his child. She decided to raise her son as a single parent with the support of her family. Rory doesn't have a good relationship with her son, which will be explained partly in this chapter, but more will explained in later chapters in detail.  
Why do this? I never expected Rory to become a great Mom/friend like Lorelai. She always had support unlike Lorelai. And also Lorelai had always been the dominant one in their relationship, making a lot of effort, Rory had always been a passive person.

Now the story moves forward with Logan finding out that he has son in the next few chapters. And how do both Rory and Logan deal with it.

I don't own Gilmore girls or it's characters. These are just my interpretations.

 **Chapter 1 - Circles**

Richard Gilmore saw circles everywhere, even in his own family.

All his family members his mother, her boyfriend and his daughter love staying indoors, comfortable with a book in their hand or watching on demand tv show on their TV or rather start a fast paced argument/mock on the stuff they watched or read.

It is like a circle, read, watch, argue, read.. It would be prepostorous of him to say that he doesn't like what they do. It is just they keep on going around the circle without ever feeling bored. He too used to like it, but it eventually lost it's sheen.

He saw the same circle in his Grandma Lorelai's life as well. Break Luke's diner rules, make Luke angry or grumpy, drink lot's of coffee, make piece with Luke, seduce Luke till he is not grumpy anymore.

He saw the same circles everywhere in Stars Hollow, his school in New York.

He sometimes felt that is what life is all about. Keep yourself in a circle which you are comfortable or happy with. Keep going around it till you die. What a load of crap!

But his restless mind couldn't accept that morbid thought. If that is what life is, he couldn't understand the point of living at all.

He always wanted more, he didn't what more is. Deepdown he knew that he will also fall into his own circle of comfort. But right now and maybe for at least a few years, he didn't want to fall into a routine. He liked trying new things, never comfortable or satisfied with what he has. In the end that is what keeps him going.

He is not unhappy about living in these circles created by his family, it's just that he wanted more. And sometimes he got it, when all these circles merge together and form one big circle, during holidays. Where everyone's routine is broken and everyone is trying to figure out their path in the newly formed circle.

It is during these times, where everything is haywire and crazy he enjoyed himself. But the most fun/ he always had is, when he broke the circles. Sometimes, those were very sad days well, but nonetheless it was always fun watching everyone of their balance. Especially his mother Rory Gilmore getting angry or flustered or sometimes make her cry(He never did anything intentionally to make her cry ). But he couldn't stop himself from doing the same thing again and again. Because he always knew that circle will form it self back again the same way it was before.

Year 2032

NewsDay Associate Editor for Arts & Books Rory Gilmore and her son Richard Gilmore(16 years old). They are not poor by any means, but they have enough money to afford live in a nice apartment with a great view overlooking forest hills. Infact his mother is a published author with two books both titled 'Gilmore Girls - Early Years' and 'Gilmore Girls - Loss of Innocence', which apparently tells his mother and Grandma Lorelai's relationship and life they had together in Stars Hollow up until his mother's graduation from Yale. Both books are moderately popular and had decent sales(Total combined sales amounted to Half-Million Copies), which is pretty good for a non-fiction book and also from a person who is not a celebrity.

Jess Mariano her boyfriend of 3 years Jess Mariano(Literary Author and publisher) lives in an apartment next block. Jess has a 13 year old daughter Liz, who is shared custody by her Mom and Dad. Most days Jess and Rory have dinner in Rory's apartment and he stays overnight most days. It is almost like he is living with them. Liz also stays with them during friday nights and weekends.

Both Liz and Richard attend public schools albeit different ones nearby their home. Strangely Jess didn't seem to like the preppy schools as well kids who study there. He always respected Jess on his ideals, a good guy. He always gave great advice to him or his own. He always made an effort to make it seem like there is no bias between his daughter and him.

But he could never experience a connection with him like he feels with his grandma Lorelai. It is like both of them are talking and living on two different wavelengths. He could never express his personal feelings to him. Their whole relationship is mostly based on mutual respect for each other. In the end, Jess is not his father, despite him being a father figure ever since he could remember things.

Actually, Richard himself doesn't know who his father is or even what his name is? Rory never mentioned him. Infact he never felt the need to know about his father, Jess in a strange way was enough. His overbearing mother is more than enough, few times he asked(in between 1st grade and 5th grade) about his father, she almost cried and told him that when the time comes, She will tell him all about his father., so he mentioned his father again, to friends in school, he tells his father is a sailor who spends most of his time travelling.

And Liz is like Jess very much in resemblance as well as in behaviour. They are mostly reticent, rather curl up in a corner and read than go out and do something crazy or have fun.

Which is quite in contrast to him and Rory. While he has his mother's eyes, he has blonde hair and very sociable and always been a trouble maker in school or at home, unlike his mother whom he was told was a model child who got perfect grades. Which didn't surprise him, his mother always had been a little bit uptight and serious.

And his relationship with his mother is simly put complicated. They don't talk much these days, when they do they get into fights. So instead they evade any meaningful conversation, just have small talk. He doesn't like share his personal life details to his anyways.

He had already been kicked out of 3 schools and going on his 4th one. And he knew that his Mom is already trying to find back up school ready if gets kicked out of this one as well. And the odds of him getting kicked out are increasing day by day.

And they are growing apart year by year mainly due to his misdemeanors. And fights between his Mom and him are becoming frequent, especially the big blowout which they had 3 months ago.

And today on a school night, he is enjoying the candy on top of him, who is topless and kneading his crotch in his bedroom.

The door swinged open, the moment he was about to enter her.

Goddamn it, he should have remembered to lock the door.

"Richard, Dinner is ready, can you reduce the volume.." His mother's voice trailed off.

But it stopped, the moment he met her eyes and saw what is happening.

She immediately shut the door. He toppled them over and got out of his bed.  
"Ow! What the hell? Get down here" Candy spoke in fake angry seductive tone. She was still lost in a fog of lust.

Oh! how he wished he met college girls sooner. And no drama like the girls in his school, and amazing flexible.

He started to look for his boxers and the rest of his clothes.  
A moment later, he heard a tapping on the door.

He groaned, this time Candy realized her surrounds and got out of his bed.

She gave him a questioning look, whether to continue or not? He gave her a regretful look.

"What is it mother?" Richard spoke in a constricted tone.

"Richard Gilmore, Dinner is served." It was her commanding voice. He knew he couldn't avoid that.

There was a pause. Both of them didn't speak.

"You can bring her along too."

Richard and Candy waited a moment, and then started getting dressed.

"I am really sorry, you don't have to sit at the table, I will make an excuse" He told her with sympathetic tone. She was bending to pickup her shirt from the floor, he looked at her backside _God! she is hot!_

"Hey! no worries Rich, If it weren't for my roommate, we wouldn't have been here in the first place. Let's just get on with it, maybe we can continue someplace else, how about the terrace, I also wanted to do it in the open".

 _Oh God! she will be the death of him. If it weren't for his mother! Ahh. Well it was his fault anyway._

"Or we can do it in the elevator, what do you think?" She quipped with a seductive tone.

He smirked at her and grabbed her by the ass bringing her close to him and bringing his lips close to her ear.

"I am up for the challenge, how about we try them both"

"I knew it the moment I met you, you are a wild one" She grinned "Lets get this over with"

As Both of them stumbled into the dinner table, they were met with silence, eyes staring at them intensely. Richard peaked at a glance at his mother and looked away. She is angry, super angry, you are grounded, I will cut your pocket-money-for-a-month angry. He is screwed. Deciding to make the best of the situation, he grabbed Candy's hand and led her to the dinner table, seated her beside him.

Rory put on a fake smile and spoke in a restrained voice.

"So Richard, care to you introduce your girl friend.." The way she uttered friend implied a lot more than she said, only Rory and Richard knew.

Richard cleared his throat "Everyone, this is candy, we met yesterday at a party. And She is not my.."

"It is Cindy" She corrected him with an annoyed tone.

Oh Oh.

He could see little Liz laughing at him. That little rascal, he always felt a connection with Liz though which is strange. Everyone else in his family according to him is serious and grumpy, but Liz showed her laid back style from time to time. And he loved that side of her. Which led him to think that maybe she got it from her mother, who is apparently in the music business.

"So Cindy is a friend" Richard stressed there making sure she is nothing more "We had been studying together. Cindy this is my mother Rory, and this is Liz, my mom's boyfriend's daughter." He gestured.

"Hi Cindy" Everyone greeted her formally.

And then there was a pause. Everyone is silent and started eating. He is happy that Jess is not here, it would have made it more awkward.

"So Cindy, Are you in my son's school, which grade are you in, cause you look a little bit older to be in his grade." Rory questioned her while having dessert.

Shit! Of all the things she could have said, this is going to be bad, if his mother finds out, he is so screwed. And also Cindy.

Cindy responded immediately.

"Oh! No I am not in his school. I am a freshman at NYU. Richard seemed interested in going to NYU, since he is in senio.."

Richard cut her off "She is pre-med mom! She has taken me to one of her classes today. You are always bugging me about what I will choose as my major when I go to college, so here I am trying out if I am interested in being a doctor. And the odds of me going pre-med are increasing." Which is obviously a lie, he couldn't have gone to Cindy class, he had school and they met at a party he sneaked into with Roger his best-friend at NYU.

"Oh! really, I thought you hate biology Cuz. What suddenly piqued your interest in the subject?" Liz questioned him with a chuckle.

She backed him into a corner, that little one, but his pride won't allow him to lose the argument. He never liked losing, especially arguments, even it meant it hurt him in the long run.

Richard wanting to make her uncomfortable, he gave her his trademark smirk "Human Anatomy, especially the fema.."

Rory interuppted him with a glare "Umm, Cindy, I am okay with you showing my 16 year old son around NYU. I mean he is just a junior in school, there are 2 more years, before he can think of.." Obviously his mother caught his lie.

Cindy dropped the spoon she is holding, with a shocked expression "Sixteen! I thought you are in your senior year" She looked at him accusingly.

"I am ..., I have an emergency, I have to go" Cindy rose from her chair.

"I am turning 17 in 9 months" He pleaded, Bad move he realized too late. Cindy glared at him and started moving towards the entrance.

He shot his own glare at his mother, who put on a fake innocent smile on her face.

"Candy wait, I can explain."

Cindy cut him off "It is over, do you have any idea how dangerous it is for me. I could go to jail"

"But I will never do that, you know that." He pleaded her with the most innocent look he could give. She almost fell for it.

"Richard, come back here" he could hear his mother's voice from the dining hall. Which brought Candy out of her thoughts.

"Whatever I am leaving, I don't want drama kid. I am scared of your mother" Just like that She left.

Richard groaned in frustration, he was about to have the craziest night of his life and his mother had just snuffed out his joy.

He went back to the table and screamed at her.

"You just ruined my night, happy?"


End file.
